US5167703A - Ink, ink-jet recording process and instrument making use of the ink - Google Patents

Ink, ink-jet recording process and instrument making use of the ink Download PDF

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Publication number
US5167703A
US5167703A US07/798,948 US79894891A US5167703A US 5167703 A US5167703 A US 5167703A US 79894891 A US79894891 A US 79894891A US 5167703 A US5167703 A US 5167703A
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United States
Prior art keywords
ink
hydrogen
water
coom
general formula
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Expired - Lifetime
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US07/798,948
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English (en)
Inventor
Tsuyoshi Eida
Mayumi Yamamoto
Takao Yamamoto
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Canon Inc
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Canon Inc
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Publication date
Priority claimed from JP33875890A external-priority patent/JP3009058B2/ja
Priority claimed from JP2338761A external-priority patent/JPH04202571A/ja
Application filed by Canon Inc filed Critical Canon Inc
Assigned to CANON KABUSHIKI KAISHA reassignment CANON KABUSHIKI KAISHA ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: EIDA, TSUYOSHI, YAMAMOTO, MAYUMI, YAMAMOTO, TAKAO
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/16—Trisazo dyes
    • C09B31/18—Trisazo dyes from a coupling component "D" containing a directive amine group

Definitions

  • the present invention relates to an ink, an ink jet recording method, and an instrument employing the ink. More particularly, the present invention relates to an ink which provides an excellent water-resistant printed image on non-coated paper, and provides a printed image having improved resistance against indoor discoloration on coated paper (paper having a pigment-coating layer), and an ink jet recording process, an ink jet device, an ink jet recording apparatus, and an ink cartridge employing the above ink.
  • ink compositions are hitherto known for ink jet recording.
  • research and development have been comprehensively made improve the composition and the properties of the ink to conduct satisfactory recording on non-coated paper such as paper for copying, paper for reporting, notebooks, letter paper, bond paper, continuous business forms, and the like.
  • inks involve the problems as below.
  • Inks generally contain a high-boiling organic solvent such as glycol for prevention of drying-up and clogging.
  • a high-boiling organic solvent such as glycol for prevention of drying-up and clogging.
  • the printed image run and become blurred, or scraped caused by sweat, a water drop, or the like, since the coloring matter used in the ink is a water-soluble dye.
  • full-color images which are printed on coated paper for forming the image clearly, come to be discolored disadvantageously even in a room where the direct sun light illumination is excluded, although sufficient light-fastness and weatherability are required to the color images.
  • the present invention intends to provides an ink which provides printed images with sufficient durability on non-coated paper, and provides printed images with little discoloration on coated paper.
  • the present invention further provides an ink jet recording method and an instrument employing the ink.
  • the present invention provides an ink comprising at least water, a water-soluble organic solvent, and a dye, the dye comprising a compound represented by the general formula (I): ##STR3## wherein R 1 , R 2 , and R 3 are respectively hydrogen or SO 3 M; R 4 is hydrogen, OCH 3 , NH 2 , NHCONH 2 , or SO 3 M; R 5 is hydrogen or SO 3 M; R 6 is hydrogen or NH 2 ; R 7 is hydrogen, CH 3 , or OCH 3 ; R 8 is hydrogen, COOM, or SO 3 M; R 5 is hydrogen and R 8 is COOM when both of R 4 and R 6 are respectively NH 2 ; M is an alkali metal, ammonium, or organic ammonium; and m is 0 or 1.
  • R 1 , R 2 , and R 3 are respectively hydrogen or SO 3 M
  • R 4 is hydrogen, OCH 3 , NH 2 , NHCONH 2 , or SO 3 M
  • R 5 is hydrogen or SO 3 M
  • the present invention also provide an ink comprising at least water, a water-soluble organic solvent, and a dye, the dye comprising a compound represented by the general formula (II): ##STR4## wherein R 1 is hydrogen, CH 3 , COOM, or SO 3 M; R 2 is hydrogen, CH 3 , or COOM; R 3 is hydrogen, chlorine, COOM, or SO 3 M; R 4 is hydrogen, OCH 3 , NH 2 , NHCONH 2 , or SO 3 M; R 5 is hydrogen or SO 3 M; R 6 is hydrogen or NH 2 ; R 7 is hydrogen, CH 3 , or OCH 3 ; R 8 is hydrogen, COOM, or SO 3 M; R 5 is hydrogen and R 8 is COOM when both of R 4 and R 6 are respectively NH 2 ; M is an alkali metal, ammonium, or organic ammonium; and m is 0 or 1.
  • R 1 is hydrogen, CH 3 , COOM, or SO 3 M
  • R 2 is hydrogen, CH 3 , or COOM
  • the present invention still also provides an ink jet recording process for conducting recording by ejecting ink droplets from an orifice in response to a recording signal, wherein the ink as described above is used.
  • the present invention further provides an ink jet device comprising an ink storing member impregnated with a recording liquid, and a head having an orifice for ejecting the recording liquid as droplets, wherein the ink as described above is used.
  • the present invention still further provides an ink jet recording apparatus comprising an ink jet device comprising an ink storing member impregnated with a recording liquid, and a head having an orifice for ejecting the recording liquid, wherein the ink as described above is used.
  • the present invention still further provides an ink cartridge comprising an ink bag impregnated with a recording liquid comprising an ink, wherein the ink as described above is used.
  • FIG. 1A and FIG. 1B illustrate a longitudinal cross section and a transverse cross section, respectively, of a head of an ink jet recording apparatus.
  • FIG. 2 is a perspective illustration of the appearance of a head having a multiple set of the heads as shown in FIG. 1A and 1B.
  • FIG. 3 is a perspective illustration of an example of an ink jet recording apparatus.
  • FIG. 4 is a longitudinal cross-sectional illustration of an ink cartridge.
  • FIG. 5 is a perspective illustration of a recording device.
  • the present invention is characterized mainly by use of a dye having a specified structure as the coloring material of ink, thereby providing an ink which gives durable printed images on various non-coated paper and gives less discoloring images on coated paper, and providing also an ink jet recording method and instruments employing the ink.
  • the dyes represented by the general formulae (I) and (II), which are used in the present invention and mainly characterizing the present invention, include any of the dyes of the above general formulae, and may be used singly or in combination of two or more thereof. Further, the dye may be used in combination with another dye which is not included in the dyes of the above general formulae.
  • the content of the dye in the ink depends on the kinds of the components of the liquid medium and the properties required to the ink. Generally, the content is in the range of from about 0.2 to about 20% by weight, preferably from 0.5 to 10% by weight, more preferably from 1 to 5% by weight of the whole ink.
  • the liquid medium used in the present invention is a mixture of water and a water-soluble organic solvent.
  • the water may be ordinary water but is preferably deionized water.
  • the organic solvent includes alkyl alcohols having 1 to 5 carbons such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, isobutyl alcohol, n-pentanol, etc., and halogenated derivatives thereof; amides such as dimethylformamide, dimethylacetamide, etc.; ketones and ketoalcohols such as acetone, diacetone alcohol, etc.; ethers such as tetrahydrofuran, dioxane, etc.; oxyethylene or oxypropylene addition products such as diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, polyprop
  • the content of the aforementioned water soluble organic solvent is generally in the range of from 2 to 50%, preferably 2 to 30% by weight of the whole ink.
  • the solvent may be used singly or in combination of two or more thereof.
  • the main constituents of the ink of the present invention is described above.
  • Other additives such as a dispersant, a surfactant, a viscosity controlling agent, a surface tention controlling agent, a fluorescent whitening agent, and the like may be added to the ink, if necessary, within the range that the object of the present invention is achieved.
  • the examples are viscosity controlling agents such as polyvinyl alcohol, cellulose derivatives; various surface active agents of cation type, anion type, and nonion type; surface tension controlling agents such as diethanolamine, and triethanolamine; pH controlling agents such as buffer solutions; mildewproofing agents; and the like.
  • a resistivity controlling agent such as inorganic salts including lithium chloride, ammonium chloride, sodium chloride.
  • the ink of the present invention is particularly suitable for an ink jet recording method of recording by ejecting ink droplets by a bubbling phenomenon upon thermal energy, and has the characteristic of stabilizing the ink ejection without causing satellite dots or other disadvantages.
  • thermal properties such as specific heat, thermal expansion coefficient, and thermal conductivity may be adjusted, if necessary.
  • the ink itself of the present invention is desirably adjusted to have a surface tension at 25° C. of from 30 to 68 dyne/cm, and a viscosity at 25° C. of not more than 15 cP, preferably not more than 10 cP, more preferably not more than 5 cP for the purpose of solving the problems of running of the ink, drying property of recorded images, and permeability of ink on non-coated paper or other recording mediums, and for the purpose of improving the matching of the ink with an ink jet head.
  • the water content in the ink of the present invention made to be in the range of from 50 to 95% by weight, preferably from 60 to 90% by weight.
  • the ink of the present invention which is particularly suitable for an ink jet recording method for recording by ejecting ink droplets by thermal energy, is naturally useful also for general writing utensils.
  • the methods and the apparatus suitable for the use of the ink of the present invention are those that provide thermal energy to ink in a cell in a recording head in correspondence with recording signals to form ink droplets by the thermal energy.
  • FIG. 1A An example of the constitution of the heads, which is a main portion of the apparatus, is shown in FIG. 1A, FIG. 1B, and FIG. 2.
  • a head 13 is formed by bonding a plate of glass, ceramics, or plastics having a groove 14 with a heat-generating head 15.
  • the type of the head is not limited to the one shown in the drawing.
  • the heat-generating head 15 is constituted of a protection layer 16 formed of silicon oxide or the like, aluminum electrodes 17-1 and 17-2, a heat-generating resistance layer 18 formed of nichrome or the like, a heat accumulation layer 19, and a substrate plate 20 having heat-releasing property made of alumina or the like.
  • Ink 21 reaches the ejection orifice 22 (a fine pore), forming a meniscus by action of pressure P not shown in the figure.
  • FIG. 2 illustrates exterior appearance of a multi-head constructed by juxtaposing a multiplicity of heads shown in FIG. 1A.
  • the multi-head is prepared by bonding a glass plate having multi-grooves with a heat-generation head 28 similar to the one described in FIG. 1A.
  • FIG. 1A is a cross-sectional view of the head 13 along an ink flow path
  • FIG. 1B is a cross-sectional view of the head at the line A-B in FIG. 1A.
  • FIG. 3 illustrates an example of the ink-jet recording apparatus having such a head mounted therein.
  • a blade 61 as a wiping member is held at one end by a blade-holding member, forming a fixed end in a shape of a cantilever.
  • the blade 61 is placed at a position adjacent to the recording region of the recording head, and in this example, is held so as to protrude into the moving path of the recording head.
  • a cap 62 is placed at a home position adjacent to the blade 61, and is constituted such that it moves in the direction perpendicular to the moving direction of the recording head to come into contact with the ejection nozzle face to cap the nozzles.
  • An ink absorption member 63 is provided at a position adjacent to the blade 61, and is held so as to protrude into the moving path of the recording head in a manner similar to that of the blade 61.
  • the aforementioned blade 61, the cap 62, the absorption member 63 constitute an ejection-recovery section 64, the blade 61 and the absorption member 63 remove water, dust, and the like from the ink ejecting nozzle face.
  • a recording head 65 has an ejection energy generation means for ejection, and conducts recording by ejecting ink toward a recording medium opposing to the ejection nozzle face.
  • a carriage 66 is provided for supporting and moving the recording head 65. The carriage 66 is engaged slideably with a guide rod 67. A portion of the carriage 66 is connected (not shown in the figure) to a belt 69 driven by a motor 68, so that the carriage 66 is movable along the guide rod 67 to the recording region of the recording head and the adjacent region thereto.
  • a paper delivery portion 51 for delivery of a recording medium and a paper delivery roller 52 driven by a motor not shown in the figure delivers the recording medium to the position opposing to the ejecting nozzle face of the recording head, and the recording medium is discharged with the progress of the recording to paper discharge portion provided with paper-discharge rollers 53.
  • the cap 62 of the ejection-recovery portion 64 is out of the moving path of the recording head 65, while the blade 61 is made to protrude into the moving path. Therefore, the ejecting nozzle face of the recording head 65 is wiped therewith.
  • the cap 62 moves to protrude toward the moving path of the recording head when the cap 62 comes into contact for capping with the ejecting nozzle face of the recording head.
  • the cap 62 and the blade 61 are at the same position as in the above-mentioned wiping time, so that the ejection nozzle face of the recording head is wiped also in this movement.
  • the recording head moves to the home position not only at the end of the recording and at the time of ejection recovery, but also at a predetermined interval during movement for recording in the recording region. By such movement, the wiping is conducted.
  • FIG. 4 illustrates an example of the ink cartridge containing ink to be supplied through an ink supplying member such as a tube.
  • the ink container portion 40 for example an ink bag, contains an ink to be supplied, and has a rubber plug 42 at the tip. By inserting a needle (not shown in the drawing) into the plug 42, the ink in the ink bag 40 becomes suppliable.
  • An absorption member 44 absorbs waste ink.
  • the ink container portion has preferably a liquid-contacting face made of polyolefin, especially polyethylene in the present invention.
  • the ink-jet recording apparatus used in the present invention is not limited to the above-mentioned one which has separately a head and an ink cartridge. Integration thereof as shown in FIG. 5 may suitably be used.
  • a recording device 70 houses an ink container portion such as an ink absorption member, and the ink in the ink absorption member is ejected from a head 71 having a plurality of orifices.
  • the material for the ink absorption member is preferably polyurethane in the present invention.
  • Air-communication opening 72 is provided to communicate the interior of the cartridge with the open air.
  • the recording device 70 may be used in place of the recording head shown in FIG. 3, and is readily mountable to and demountable from the carriage 66.
  • solid printing was conducted by means of a recording apparatus (BJ-130, made by Canon K.K.) having an On-Demand type of multiple orifice head for conducting recording by giving heat energy to the ink in the recording head to form liquid droplets, thus preparing printed pieces in the size of 10 ⁇ 20 mm.
  • the test paper used were paper recommended for Canon NP-6150, Canon NP-Dry, Noizidlerpaper, and Proberbond paper.
  • the optical densities of the printed matters were all within the range of from 1.30 to 1.45.
  • the water resistance of the print was evaluated by immersing the printed piece in stagnant water at 20° C. for 5 minutes and then measuring the degree of decrease of the optical density.
  • solid printing was conducted by means of a recording apparatus (BJ-130, made by Canon K.K.) having an On-Demand type of multiple orifice head for conducting recording by giving heat energy to the ink in the recording head to form liquid droplets, thus preparing printed pieces in the size of 10 ⁇ 20 mm.
  • the test papers used were papers recommended for Canon NP-6150, Canon NP-Dry, Noizidlerpaper, and Proberbond paper.
  • the optical densities of the printed matters were all within the range of from 1.30 to 1.45.
  • the water resistance of the print was evaluated by immersing the printed piece in stagnant water at 20° C. for 5 minutes and then measuring the degree of decrease of the optical density.
  • Inks (a) to (e) were prepared in the same manner as in Example 1 except that the dyes were changed respectively to the mixture having the composition as below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Pens And Brushes (AREA)
US07/798,948 1990-11-30 1991-11-27 Ink, ink-jet recording process and instrument making use of the ink Expired - Lifetime US5167703A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2-338758 1990-11-30
JP33875890A JP3009058B2 (ja) 1990-11-30 1990-11-30 インク、これを用いたインクジェット記録方法及びかかるインクを用いた機器
JP2-338761 1990-11-30
JP2338761A JPH04202571A (ja) 1990-11-30 1990-11-30 インク、これを用いたインクジェット記録方法及びかかるインクを用いた機器

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US (1) US5167703A (de)
EP (1) EP0490195B1 (de)
AT (1) ATE167222T1 (de)
DE (1) DE69129578T2 (de)
ES (1) ES2116990T3 (de)

Cited By (23)

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US5415686A (en) * 1993-04-07 1995-05-16 Canon Kabushiki Kaisha Ink, ink-jet recording method making use of the same and instrument provided with the ink
US5429671A (en) * 1993-03-12 1995-07-04 Canon Kabushiki Kaisha Ink, and ink-jet recording method and apparatus employing the ink
US5451251A (en) * 1993-02-26 1995-09-19 Canon Kabushiki Kaisha Ink, and ink-jet recording method and instrument using the same
US5466282A (en) * 1993-05-18 1995-11-14 Canon Kabushiki Kaisha Azo dye compound, ink containing the same, and recording method and instrument using the ink
US5482546A (en) * 1994-03-30 1996-01-09 Canon Kabushiki Kaisha Dye, ink containing the same, and ink-jet recording method and instrument using the ink
US5482545A (en) * 1993-12-28 1996-01-09 Canon Kabushiki Kaisha Ink, and ink-jet recording method and instrument using the same
US5500023A (en) * 1993-04-21 1996-03-19 Canon Kabushiki Kaisha Ink-jet printing process, ink set for use in such process, and processed article obtained thereby
US5686951A (en) * 1992-08-10 1997-11-11 Canon Kabushiki Kaisha Ink jet printing method and printed article
US5728201A (en) * 1995-09-14 1998-03-17 Canon Kabushiki Kaisha Ink, and ink-jet recording method and instruments using the same
US6003987A (en) * 1992-09-17 1999-12-21 Canon Kabushiki Kaisha Ink set recording apparatus and method using ink set having a dye that becomes insoluble when mixed with another dye
US6281917B1 (en) 1997-04-01 2001-08-28 Canon Kabushiki Kaisha Image forming process employing liquid composition and ink in combination
US6478862B1 (en) 2000-03-14 2002-11-12 Macdermid Acumen, Inc. Pigmented inks and a method of making pigmented inks
US6715868B2 (en) 2001-02-16 2004-04-06 Macdormid Colorspan, Inc. Direct dye inks and a method of making direct dye inks
US20060192826A1 (en) * 2005-02-28 2006-08-31 Canon Finetech Inc. Ink-jet water-based ink, ink-jet recording method, ink cartridge and ink-jet recording apparatus
US20070032570A1 (en) * 2003-11-11 2007-02-08 Canon Kabushiki Kaisha Ink comprising a block copolymer dispersing agent having a hydrophilic and a hydrophobic segment and an ink-applying process and apparatus using the same
US20070105980A1 (en) * 2005-11-07 2007-05-10 Canon Finetech Inc. Ink jet aqueous ink, ink jet recording method, ink cartridge and ink jet recording apparatus
US7285160B2 (en) 2003-11-04 2007-10-23 Videojet Technologies Inc. Ink jet ink composition for wetness indication
EP2457955A1 (de) * 2010-11-30 2012-05-30 Kemira Oyj Trisazo-Farbstoffe für Papierfärben
CN103237847A (zh) * 2010-11-30 2013-08-07 凯米拉公司 偶氮染料
US8876962B2 (en) 2011-09-08 2014-11-04 Canon Kabushiki Kaisha Aqueous ink, ink cartridge, and ink jet recording method
US9187662B2 (en) 2012-03-02 2015-11-17 Canon Kabushiki Kaisha Ink, ink cartridge and ink jet recording method
US9809721B2 (en) 2015-01-23 2017-11-07 Canon Kabushiki Kaisha Aqueous ink, ink cartridge, and ink jet recording method
US10253200B2 (en) 2015-01-23 2019-04-09 Canon Kabushiki Kaisha Aqueous ink, ink cartridge, and ink jet recording method

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JP3162834B2 (ja) * 1991-10-25 2001-05-08 レックスマーク・インターナショナル・インコーポレーテツド 耐水性染料および水性インク
EP0656407B1 (de) * 1993-11-29 1999-03-03 Mitsubishi Chemical Corporation Aufzeichnungsflüssigkeit
US5948150A (en) * 1998-05-05 1999-09-07 Hewlett-Packard Company Composition to improve colorfastness of a printed image
TWI561588B (en) * 2011-10-22 2016-12-11 Archroma Ip Gmbh Trisazo acid dyes
MX2017010901A (es) * 2015-03-16 2017-11-24 Archroma Ip Gmbh Colorantes de acido trisazo.

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US4670548A (en) * 1979-04-14 1987-06-02 Bayer Aktiengesellschaft Sulfo-group-containing trisazo dyestuffs
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Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5686951A (en) * 1992-08-10 1997-11-11 Canon Kabushiki Kaisha Ink jet printing method and printed article
US6003987A (en) * 1992-09-17 1999-12-21 Canon Kabushiki Kaisha Ink set recording apparatus and method using ink set having a dye that becomes insoluble when mixed with another dye
US5451251A (en) * 1993-02-26 1995-09-19 Canon Kabushiki Kaisha Ink, and ink-jet recording method and instrument using the same
US5429671A (en) * 1993-03-12 1995-07-04 Canon Kabushiki Kaisha Ink, and ink-jet recording method and apparatus employing the ink
US5415686A (en) * 1993-04-07 1995-05-16 Canon Kabushiki Kaisha Ink, ink-jet recording method making use of the same and instrument provided with the ink
US5500023A (en) * 1993-04-21 1996-03-19 Canon Kabushiki Kaisha Ink-jet printing process, ink set for use in such process, and processed article obtained thereby
US5466282A (en) * 1993-05-18 1995-11-14 Canon Kabushiki Kaisha Azo dye compound, ink containing the same, and recording method and instrument using the ink
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US10253200B2 (en) 2015-01-23 2019-04-09 Canon Kabushiki Kaisha Aqueous ink, ink cartridge, and ink jet recording method

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DE69129578D1 (de) 1998-07-16
ES2116990T3 (es) 1998-08-01
EP0490195B1 (de) 1998-06-10
EP0490195A1 (de) 1992-06-17
ATE167222T1 (de) 1998-06-15
DE69129578T2 (de) 1998-10-15

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